Iridium-Catalyzed Dehydrogenative Aromatization of Cyclohexanols and Cyclohexanones to Phenols
Zhaozi Lv , Kuan Wang , Juntao Liu , Guixia Liu , Lan Gan , Zheng Huang
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (19) : 2465 -2470.
Iridium-Catalyzed Dehydrogenative Aromatization of Cyclohexanols and Cyclohexanones to Phenols
Catalytic dehydrogenative aromatization (CDA) has emerged as a powerful strategy for the synthesis of substituted phenols. However, most of the known CDA methods suffer from limited functional group compatibility due to the use of strong oxidants, reductants, or bases. Herein, we report a (cis-P2Cl)Ir-catalyzed CDA reaction enabled by transfer dehydrogenation (TD). This catalytic system is effective for CDA of both cyclohexanone and cyclohexanol derivatives and demonstrates excellent tolerance toward a variety of functional groups, including readily oxidizable electron-rich heterocycles. DFT studies further reveal that the (cis-P2Cl)Ir catalyst is thermodynamically disfavored for the formation of a potential out-of-cycle catalyst species, iridium phenoxyl hydride complex, via oxidative addition of the phenol O–H bond, thereby preventing catalyst inhibition observed in the previously reported TD system.
Dehydrogenative aromatization / Transfer dehydrogenation / Preparation of substituted phenol / Cyclohexanone / Cyclohexanol
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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